Water → 2-bromo-1-(8-bromo-6H-dibenzo[c,h]chromen-2-yl)ethanone

HRID 1751529ノート

反応式

HRID 1751529 の反応式
FC(F)(F)S(O[C:7]1[CH:8]=[CH:9][C:10]2[C:11]([CH:25]=1)=[CH:12][CH:13]=[C:14]1[C:19]=2[O:18][CH2:17][C:16]2[CH:20]=[C:21]([Br:24])[CH:22]=[CH:23][C:15]1=2)(=O)=O.C([Sn](CCCC)(CCCC)[C:33]([O:35]CC)=[CH2:34])CCC.O.[Br:47]N1C(=O)CCC1=O>CN(C)C=O.ClCCl.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Br:47][CH2:35][C:33]([C:7]1[CH:8]=[CH:9][C:10]2[C:11]([CH:25]=1)=[CH:12][CH:13]=[C:14]1[C:19]=2[O:18][CH2:17][C:16]2[CH:20]=[C:21]([Br:24])[CH:22]=[CH:23][C:15]1=2)=[O:34]

参加物

8

反応物 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 867087538-bromo-6H-dibenzo[c,h]chromen-2-yl trifluoromethanesulfonate

生成物 1

HCID 867087542-bromo-1-(8-bromo-6H-dibenzo[c,h]chromen-2-yl)ethanone収率 70.5%

試薬・触媒・溶媒 3

HCID 11071931Dichloropalladium--(ethane-1,2-diyl)bis(diphenylphosphane) (1/1)触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 8-bromo-6H-dibenzo[c,h]chromen-2-yl trifluoromethanesulfonate (780 mg, 1.7 mmol) and tributyl(1-ethoxyvinyl)stannane (0.86 mL, 2.6 mmol) in dimethylformamide was degassed with a stream of argon for 15 minutes. PdCl2(dppe) (50 mg, 0.086 mmol) was added and the reaction was stirred at room temperature. After 30 hours, water (1 mL) and N-bromosuccinimide (756 mg, 4.2 mmol) were sequentially added to the reaction. After stirring for 2.5 hours at room temperature the reaction was diluted with dichloromethane. The organics were washed with 5% aqueous LiCl solution, saturated aqueous NaHCO3 solution, and brine. After the organic layer was dried (Na2SO4) and concentrated, the crude material was recrystallized from dichloromethane and hexanes to yield 2-bromo-1-(8-bromo-6H-dibenzo[c,h]chromen-2-yl)ethanone (518 mg, 57%).

後処理

  1. stirringAfter stirring for 2.5 hours at room temperature the reaction
  2. washThe organics were washed with 5% aqueous LiCl solution, saturated aqueous NaHCO3 solution, and brine
  3. dry with materialAfter the organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe crude material was recrystallized from dichloromethane and hexanes

出典と根拠

ORDレコード
ord-6f84fc2e1150415b8872acdfd91b5397
出典データセット
uspto-grants-2015_10
特許番号
US09156823B2

反応ノート

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